Poly(aryl ether) based polymers and associated gas separation membranes

Abstract

Compositions and methods related to the synthesis and application of poly(aryl ether)s are generally described.

What is claimed is: 
     
       1. A method of making a gas separation membrane comprising a poly(aryl ether), comprising:
 providing a first prepolymer comprising a monomer of a formula (X) x —Ar—(OH) y , wherein Ar comprises at least one aryl or heteroaryl group, X is a halogen or a halogen equivalent, each X is the same or different, and x+y is at least two; 
 providing a second prepolymer comprising a comonomer of a formula (X) x —Ar′—(OH) y  wherein Ar′ comprises at least one aryl or heteroaryl group, X is a halogen or a halogen equivalent, each X is the same or different, and x+y is at least two; 
 providing a catalyst; 
 providing a base; 
 reacting the first prepolymer with the second prepolymer in the presence of the catalyst and the base to provide the poly(aryl ether); and 
 forming the gas separation membrane. 
 
     
     
       2. The method of  claim 1 , wherein the poly(aryl ether) is of a formula [(—Ar—O—Ar′—O—) n ] or [(—Ar′—O—Ar—O—) n ], wherein n is greater than 1. 
     
     
       3. The method of  claim 1 , wherein the halogen is bromide, chloride, and/or iodide. 
     
     
       4. The method of  claim 1 , wherein the catalyst comprises a metal. 
     
     
       5. The method of  claim 4 , wherein the metal is palladium, nickel, or iron. 
     
     
       6. The method of  claim 1 , further comprising:
 providing a third prepolymer comprising a second comonomer of a formula (X) x —Ar″−(OH) y , wherein Ar″ comprises at least one aryl or heteroaryl group, X is a halogen or a halogen equivalent, each X is the same or different, and x+y is at least two, and 
 reacting the first prepolymer with the second prepolymer and the third prepolymer in the presence of the catalyst and the base to provide the poly(aryl ether). 
 
     
     
       7. The method of  claim 6 , wherein the poly(aryl ether) is of a formula [(—Ar′—O—Ar—O—Ar″—O—) n ] or [(—Ar″—O—Ar—O—Ar′—O—) n ], wherein n is greater than 1. 
     
     
       8. The method of  claim 1 , further comprising:
 providing an endcapping agent; and 
 reacting the first prepolymer with the second prepolymer and the endcapping agent in the presence of the catalyst and the base to provide the poly(aryl ether). 
 
     
     
       9. The method of  claim 8 , wherein the poly(aryl ether) is of a formula [(—Ar—O—Ar′—O—) n EC], [EC(—Ar—O—Ar′—O—) n ], [EC—O—Ar′(—Ar—O—Ar′—O—) n EC], [(—Ar′—O—Ar—O—) n EC], [EC(—Ar′—O—Ar—O—) n ], [EC(—Ar′—O—Ar—O) n —Ar′—EC], [EC(—Ar—O—Ar′—O—) n Ar—EC], or [EC(—Ar′—O—Ar—O—) n EC], wherein n is greater than 1 and EC is the endcapping agent. 
     
     
       10. The method of  claim 8 , wherein the endcapping agent comprises an alkyne, a polymer, a cyclic group, a heterocyclic group, and/or a nanoparticle. 
     
     
       11. The method of  claim 8 , wherein the endcapping agent comprises norbornene. 
     
     
       12. The method of  claim 1 , further comprising functionalizing the poly(aryl ether). 
     
     
       13. The method of  claim 12 , wherein the poly(aryl ether) is functionalized by halogenation, sulfonation, nitration, acylation, nitrene addition, carbene addition, radical addition, and/or chloromethylation. 
     
     
       14. The method of  claim 1 , wherein Ar and/or Ar′ comprises a benzene group, a phenanthrene group, an iptycene group, a spirobi(indene) group, a fluorene group, a spirobifluorene group, a pyridine group, a bipyridine group, a phenanthroline group, a cyclopentane group, and/or a bicyclic ring structure, any of which may be optionally substituted.